243982-82-3Relevant articles and documents
Synthesis of polybrominated diphenyl ethers and their capacity to induce CYP1A by the Ah receptor mediated pathway
Chen,Konstantinov,Chittim,Joyce,Bols,Bunce
, p. 3749 - 3756 (2007/10/03)
Polybrominated diphenyl ethers (PBDEs) have become widely distributed as environmental contaminants due to their use as flame retardants. Their structural similarity to other halogenated aromatic pollutants has led to speculation that they might share toxicological properties such as hepatic enzyme induction. In this work we synthesized a number of PBDE congeners, studied their affinity for rat hepatic Ah receptor through competitive binding assays, and determined their ability to induce hepatic cytochrome P-450 enzymes by means of EROD (ethoxyre-sorufin-O-deethylase) assays in human, rat, chick, and rainbow trout cells. Both pure PBDE congeners and commercial PBDE mixtures had Ah receptor binding affinities 10-2-10-5 times that of 2,3,7,8-tetrachlorodibenzo-p-dioxin. In contrast with polychlorinated biphenyls, Ah receptor binding affinities of PBDEs could not be related to the planarity of the molecule, possibly because the large size of the bromine atoms expands the Ah receptor's binding site. EROD activities of the PBDE congeners followed a similar rank order in all cells. Some congeners, notably PBDE 85, did not follow the usual trend in which strength of Ah receptor binding affinity paralleled P-450 induction potency. Use of the gel retardation assay with a synthetic oligonucleotide indicated that in these cases the liganded Ah receptor failed to bind to the DNA recognition sequence.
Synthesis and characterization of 32 polybrominated diphenyl ethers
Marsh, Goeran,Hu, Jiwei,Jakobsson, Eva,Rahm, Sara,Bergman, Aeke
, p. 3033 - 3037 (2007/10/03)
Polybrominated diphenyl ethers (PBDEs) are widely used as additive flame retardants in, for example, textiles, computers, television sets, and other electrical appliances. present also in humans. The environmental levels of the PBDEs are, however, still in general lower than those of polychlorinated biphenyls (PCBs). However, while the levels of PCBs generally are decreasing, those of the PBDEs are increasing in, for example, human milk. In the present study 32 individual PBDE congeners were synthesized and characterized. Physicochemical parameters including melting points and UV, 1H NMR, and mass spectra are reported Twenty-nine monobrominated to heptabrominated diphenyl ethers were synthesized by the couping between four diphenyliodonium salts and nine phenolates. One tetrabromodiphenyl ether and two hexabromodiphenyl ethers were synthesized by bromination of two different PBDEs. Twenty-one of the PBDEs and two of the iodonium salts, 2,2′,4,4′-tetrabromodiphenyliodonium chloride and 3,3′,4,4′-tatrabromodiphenyliodonium chloride, are to the authors' knowledge described for the first time. These synthesized reference compounds will aid in the identification and quantification of PBDEs present in environmental samples and will allow further assessment of PBDE toxicity.